In a recent op-ed, author Howard Jacobson argues that satire is among the most potent forms of criticism. Writing about the recent play that recast Julius Caesar as a parody of Donald Trump, Jacobson wrote that “wounding the vainglorious is a pleasing pastime in itself and contributes to their demoralization.”

“Their solemn edifices start to crumble,” he continued in his op-ed for the New York Times. “It might be a slow process, but it is at least the beginning.”

Basically, if we clown Trump enough, he’ll break.

On Monday night, Jordan Klepper will try a variation of that philosophy with his new show, The Opposition, which the Times deemed “The Colbert Report for the Breitbart era.”

Indeed, it will be difficult for Klepper’s show, which will parody the personalities and perspectives of the “alt-right,” to escape the Colbert comparisons.

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But setting itself apart from the late-night contributions of its predecessors and its contemporaries may actually be the least of The Opposition’s challenges. Whether this particular brand of satire can fly at this current moment is one obvious concern. But equally worrisome is what a success of the show could mean for the alt-right it seeks to mock.

The New Yorker’s Andy Borowitz has called the Trump era an age that “defies satire.” In an interview with CNN, the satirist said that the administration posed a challenge to satirists in particular. Satire typically relies on exaggeration in order to help the audience recognize the folly, the ridiculousness, of a situation.

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As Borowitz tells his interviewer, Brian Stelter, it’s difficult to “one-up the alt-right.”

It’s difficult to exaggerate Trump’s awfulness: his racism, his incompetency, his bold lack of interest in the business of governing. It’s arguably even harder to then turn up the volume on the people who support him: white nationalists, conspiracy theorists and militants.

Still, satire is alive and well in the U.S.—albeit in an entirely different landscape than the one Stephen Colbert entered into when TheColbert Report debuted in 2005.

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Borowitz has continued to write sharp, witty pieces for the New Yorker, and Twitter is awash with concise, cutting takes on the president and his administration. Writers like Jason O. Gilbert, “Black Aziz Ansari,” Megan Amram and Shaun Lau provide the quick comic cut so many of us need when scrolling through our news feeds.

Therein lies some of the challenge: Klepper and his team, like Colbert and like TheDaily Show, will need to perform this comedic tightrope for 30 minutes, five nights a week.

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As Borowitz told CNN, “It’s really tough to make a daily diet of comedy out of something that’s already ridiculous.”

And there’s good reason to believe that not only will the alt-right love it, but the spotlight The Opposition shines on the political grouping could very well help it grow.

In keeping with the format of The Daily Show, The Opposition will be anchored by Jordan Klepper and will feature segments from six “citizen journalists”—all of whom come from an improv background.

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Last week, at a press event, Klepper introduced the team. Two young white men will play the role of Milo Yiannopoulos-esque troll-provocateurs thirsting for fame. Niccole Thurman will play a black “party girl” who supports Trump out of unabashed self-interest. In introducing Thurman, Klepper noted that he found it great that she did not come at her character from “an identity politics” perspective. Rounding out the cast is an articulate bullshitter, a “beta male” and a loud and proud “heartland woman” who is, essentially, an anti-feminist feminist.

Out of the seven comics, two are women and two are black, which perhaps makes sense given that the show is supposed to represent the alt-right. But it’s also just what late-night TV looks like.

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I asked Klepper about the challenges of making satire at this particular moment. While he acknowledged the challenge, he also felt it a necessity to play with these issues and personalities.

“You’re starting to see that certain things that feel so outlandish and felt so fringe at one point have now become so mainstream,” Klepper said. “You read these headlines that I feel like there’s so much face-palming going on, you’re like, ‘What is a new way about this?’”

Of course, if you’re a person of color, the sort of casual racism espoused freely by a lot of the alt-right was never a fringe element. Many of us are all too familiar with racism as a mainstream phenomenon, and while there were moments when The Daily Show and Colbert excelled at satire that confronted race, there were plenty of moments in the shows’ histories where their jokes fell flat.

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The Opposition set also features a mock conspiracy theory bulletin board. Cutouts of Beyoncé with a reminder to “buy tickets” feature, as do Hillary Clinton and Taylor Swift. In a corner, an index card reads, “It’s only news if you believe it,” a sentiment that, if you’ve ever encountered a Kinja commenter, doesn’t feel like parody at all.

In fact, some may argue that attempting to treat these perspectives passively, through humor, could diffuse the impulse to fight them.

A 2013 essay from Jonathan Coe in the London Review of Books raises a troubling prospect in an age where people need to protest vociferously just to hold on to health care. Satire, Coe argues, “is not just ineffectual as a form of protest, but that it actually replaces protest.”

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This is because of the comedian’s special gift for defusing tense situations. When a joke works, the audience relaxes and releases anxiety. It feels great to clown your enemies, but the problem is, it may feel too good.

Of course, the point of comedy isn’t to change minds. But even if you don’t buy the argument that laughter negates protest, there is another aspect to satire that we must reckon with: Your enemies are laughing, too. And in 2017, if you’re satirizing the alt-right, they’re taking that laughter and churning out content.

In an interview with Business Insider, Infowars editor and culture-wars vlogger Paul Joseph Watson explained how The Opposition could create an instant feedback loop for the very personalities it satirizes. He also took the parody show as a sort of badge of honor.

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“The fact that they have to resort to satirizing me in a comedy show proves that they’re struggling to combat me with actual logical arguments,” Watson told BI.

In fact, Watson’s comments made clear that TheOpposition would provide material that would be funneled back onto the site: a symbiotic relationship where coverage generates content.

“I am getting under their skin, and I love it,” he said. “I look forward to seeing the show and will no doubt be able to mine it for a ton of great content.”

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When I asked Klepper if he feared that airing those far-right views might further mainstream them, the late-night host pointed out that a lot of those beliefs are already mainstream.

“They’re flowing downstream. You see it on Hannity, you see Donald Trump tweet it out. So we are trying to see what things are taking hold and where that paranoia begins,” Klepper said. “But if something feels too fringe or too hateful and it’s not a part of the conversation, that’s the stuff that we, we’re not interested in that.”

Which raises the issue: When talking about the far right, a group that has virulently called for Hillary Clinton’s death, that regularly dehumanizes black celebrities and frames white nationalists as guardians, what exactly would a satirist deem too hateful?

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That symbiotic relationship between a satirist and his subject could explain one of the more troubling effects of The Colbert Report.

Malcom Gladwell called it “the Satire Paradox” in a recent episode of his podcast, Revisionist History: Satire often pleases and appeases the very people it’s mocking.

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Take Colbert, whom the Los Angeles Times called “America’s satirist laureate” back in 2014, as his show was ending. An Ohio State study showed that conservatives who watched Colbert didn’t believe the talk show host was mocking them. They were laughing along with Colbert, precisely because they felt Colbert was secretly with them.

In fact, another study (composed predominantly of young white men) found that watching The Colbert Report complicated those viewers’ understanding of politics. After watching the show, the students surveyed were more likely to agree with the statement, “Sometimes politics and government seem so complicated that a person like me can’t really understand what’s going on.”

The same study found that TheColbert Report—like The O’Reilly Factor, one of the talk shows Colbert was parodying—made those students more sympathetic to conservative viewpoints.

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It’s a troubling thought: that a show intended to shine a light on the folly of the alt-right could further animate it. To remedy this, Gladwell suggests that “satire works best when the satirist has the courage not just to go for the joke.”

Great comedy is a curious alchemy: that perfect combustion of writing, timing, perspective and delivery that can be every bit an awakening force as much as a salve. Klepper and his team will see Monday night how well their jokes land, from whom they’re drawing laughs and what, exactly, their brand of satire can offer in an age that defies it.